4-Fluorobenzaldehyde → HCID 178453963, compound

HRID 1024812Notes

Reaction equation

[C:1]([O:5][C:6](=[O:33])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14](=[O:32])[NH:15][C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].F[C:35]1[CH:42]=[CH:41][C:38]([CH:39]=[O:40])=[CH:37][CH:36]=1>>[C:1]([O:5][C:6](=[O:33])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14](=[O:32])[NH:15][C:16]2[CH:21]=[C:20]([O:22][C:35]3[CH:42]=[CH:41][C:38]([CH:39]=[O:40])=[CH:37][CH:36]=3)[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 680234-Fluorobenzaldehyde

HCID 178453966HCID 178453966, compound

Product 1

HCID 178453963HCID 178453963, compoundYield 32.6%

Procedure

Following the procedure of Example 42(b) {trans-4-[3-(4-cyano-phenoxy)-5-hydroxy-phenylcarbamoyl]-cyclohexyl}-carbamic acid tert-butyl ester (1.0 g, 2.21 mmol) and 4-fluorobenzaldehyde (0.475 ml, 4.43 mmol) were used to afford 0.4 g of the required product. 1H NMR (DMSO-d6): δ 1.11 (4H, m), 1.29 (9H, s), 1.8 (4H, m), 2.11 (1H, m), 3.15 (1H, m), 6.82 (1H, d), 7.34 (6H, m), 7.86 (2H, d), 7.92 (2H, d), 10.11 (1H, s).

Sources & evidence

ORD record: ord-d428c26577f8456295471ad57f21f313
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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